The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor, is described; the γ-lactam portion possessing a quaternary carbon in 1 was constructed stereoselectively from D-glucose using the allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.
N. Chida, J. Takeoka, N. Tsutsumi and S. Ogawa, J. Chem. Soc., Chem. Commun., 1995, 793 DOI: 10.1039/C39950000793
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